The History Boo

Character introduction:

MC = Jack

Mom = Carine

Dad = Robert/Cassandra

Sister = Anne

Sissy femboy girlfriend = Matt

Colombian girlfriend = Cecilia

Irish friend = Maeve O'Callaghan

Argentine girl = Victoria

Maty's mom = Stephanie

Cecilia's mom = Mabel

Cecilia's older twin sisters = Amanda and Maria

Cecilia's aunt = Sandra

Sandra's three daughters = Casiopea, Belen, and Celeste.

Ebony beauty = Candy

Maeve's mothers = Pilar and Hailey

Mayor's nephew = Mike

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All characters are 18 or older.

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Chapter 23, reaching out and pulling in.

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Stephanie drove herself wild since the fight. She saw her son's boyfriend beat that bulking black man on the ring with the grace of a dancer and the strength of Hercules.

She went home without her son, since he wanted to celebrate with his Man... or Daddy... the mom wasn't really sure of their relationship but was ok with it since Jack seemed upfront and not abusive, he was way more mature than she thought a boy his age should be.

From the conversations they shared before he always seemed in control and quick on his feet.

'If only I was 10 years younger...'

she thought with some shame about her thoughts for her son's boyfriend.

"Still, the new friendships are nice." She surmised, thinking of Carine, Cassandra, and Anne. The four quickly became friends as her son began to openly crossdress and wear make up.

They were great support for Maty, and her, as they navigated the relationship Jack threw Maty into and the new life her son chose for himself.

"Still, I can't believe the way his ass fits on those shorts..."

The night of the fight, when she went home and realized she was alone, Stephanie decided for a quick me-time session and flopped herself on the bed with her usual videos of 8', 9', and 10' cocks ramming some milf in whatever superficial plot.

When she finished, feeling frustrated and annoyed, fantasizing of a partner with the size she desperately needed; she left her room to catch up on some chores.

As she walked past her son's room, she saw his laptop open from the edge of her vision and had to do a double take.

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"Maeve! What a nice surprise!" Exclaimed Cassandra as she opened the door. Maeve had chosen a tight tube top and even tighter short shorts in orange and blue with orange high heels and an orange purse, she giggled and exclaimed with the same enthusiasm back at Cassandra before they hugged.

"Hurry up, girl! I don't wanna miss the show!" Cassandra said, pulling Maeve inside.

"What show?" The bimbo asked, but her question was answered when Cassandra brought her to the kitchen window, "ooohhh, spicy!"

Cassandra pulled the top of her dress down and the bottom of her dress up in a tight tube around her tummy, retaking her position to finger her ass-pussy and fondle her tits.

Maeve didn't feel like disturbing, so she did the same and began masturbating next to Jack's T-MILF, "I love coming to this house!" She said, pulling a light giggle from Cass.

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Jack fucked his mother to several squirting orgasms, and dumped another heavy load inside of her. She moaned in an exhalation and kissed her son one final time. He stood as tall as he was and turned to the threesome on the lounge chair. He whistled and called the three to his attention.

Maty and Cecilia flew to his arms and the three shared a kiss as Jack fondled and mauled their bodies, Anne catwalked to them last and joined in the hug.

"Anne, you have a big creampie there to take care of," Jack informed her and she giggled and knelt between her mother's open legs.

"How are you taking this, you two?" He then asked his girlfriends. Cecilia and Maty looked at each other again, they felt Jack's cum dripping between their legs, and the arousal muddled their replies, but the moment Jack stopped the game to ask them how they were, made them both happy and warm.

"I never expected you meant your mom and sister, Daddy..." Maty began, Cecilia grabbed his arm and added, "not in a million years!"

He chuckled back at them, "I guess it was inevitable, and to be honest I kinda was hoping it would be that way..." finished Maty, Cecilia nodded in her place.

"So, you guys are ok with this?" Jack asked again. It was now time for Cecilia to speak.

"I feel it's not my place, you offered me this life and I accepted. Still, you weren't joking when you said you are greedy."

Maty snorted and Jack chuckled again, "I want this, and I want you both as well... and I know you want what I'm planning. The only question now is, where's the line?" He finished, caressing both his girlfriends backs, as they heard the moans from Carine behind them.

Maty placed a hand on Jack's chest, "we talked... and we are ready. You choose the line Jack." The sissy looked up at Jack, his big doe eyes shining with their clear blue.

Jack leaned down and kissed the sissy, his hand snaking down and pinching with index finger and thumb the sissy's small hard boy-clit. He moaned and stood on his toes, leaning against his man, as he jerked him a little. The small femboy shuddered right as Jack turned for Cecilia and kissed her, his hand finding her pussy with two fingers probing her entrance.

The Latina for her part, wrapped her arms around his neck and held her man tight, "thank you, Jack. Let's be happy together..."

"You mean the three of us, or everyone I plan to bring?" He replied with a chuckle.

""All of us!"" Stated both the sissy and the latina at the same time.

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Anne licked and lapped her own mother's pussy with eased practice. She held her thick thighs as she munched, licked, nipped, and bit, the pussy that brought her to this world.

She wondered for a moment what Jack was doing, but she trusted him deeply. He is the center of her life, whatever he decides to do, she supports wholeheartedly. Still, she moved her bubble butt side to side enticingly in the hopes he looked at her. If not, she was happy to enjoy this moment with her mother. Anne, Carine, and Cassandra considered each other sister-wives to Jack. Carine and Anne found their place caring for the home at his pleasure, Cassandra found it working and making money.

The three knew Jack would do whatever he wanted and they wanted to support that, just be happy at his side.

She jumped a little when she felt a hand spanking her, she recognized those hands, the slow caress over her skin and the rough yet gentle hold on her hips as he placed his cock at her entrance and pushed inside.

"YES! FUCK ME DADDY!" She yelled as he penetrated her fully, like no other man could. She knew.

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Jack began pumping in and out of his sister's pussy, he was relaxed, sawing in and out at a leisurely pace. Cecilia knelt next to him and his hand found her pussy once again, she moaned in between kissing his side.

Maty for his part realized he had several orgasms, yet he was hard, his less than three inches boy clit pointing up. He glued his body up to Jack's, rubbing his hips against Jack's thigh. The daddy for his part slid his hand down and with two fingers penetrated the sissy's ass-pussy.

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"Oh, God! Look at Daddy fuck them!" Maeve moaned, as she fingered her pussy and fondled her breasts. Cassandra moaned her agreement doing the same, as her little shrunken penis throbbed.

Maeve wanted desperately to join the fivesome by the pool, but Jack had made it clear to her that he decided when he fucked anyone, (although he never said it), and she would wait until he decided to let her join, (and it probably was a good idea, since Jack forgot Maeve was even coming).

The two watched Jack fuck his girlfriends, mommy, and sister one more time each, spanking, fondling, and kissing everyone's profusely to the point that each of the four laid flat on their back on the tiled floor, gasping, and drenched in sweat; cum pouring out of their pussies and ass-pussy.

From the window, they heard Jack speak.

"I'm thirsty, I'll be right back..." and he stood naked and walked back to the kitchen.

When he turned and paced back, Cass and Maeve saw him move in slow motion, his glistening body, his dangling member, his hair and muscles.

The man walked into the kitchen and found the two bent over the kitchen counter, looking out the window, he peaked out the window and saw they had a straight line to the lounge chairs and the pool, where he had his fivesome.

"You like peeping over the window, perverts?" he commented, making Cass and Maeve moan about their agreement. The two turned to him, rubbing his body in the way a puppy smoders his owner after a long day. The two brought themselves to their respective orgasms several times, yet it was only Cassandra that realized how long they've been engaged, it was past lunchtime now.

"Tell you what! I'm thirsty, so you can suck my cock as I drink..." he chuckled, and the two knelt on the ground looking up at him with puppy eyes and whispered thank yous.

Jack filled a glass and brought it to his mouth without thinking, while his

pets

crawled closer. Maeve simply opened her mouth, tongue out and placed his cock head at the entrance, drawing circles with her tongue, while Cassandra pressed her face against his ball sack to sniff in his scent and kiss the heavy testicles.

three gulps was all it took for the glass to be finished, so Jack simply willed another erection up.

Both Cassandra and Maeve giggle and cheer for Jack's virility.

Jack's phone rang in the living room, he coordinated with the two at his feet and the three got there. He answered the phone as he sat on the couch and opened his legs wide to give the two access, who resumed their ministrations on his turgid member.

"Yes?" Jack answered the phone, as Maeve pushed forward taking the cock past her throat with the practiced ease of Queen of Hearts in love, his trans-mom lapped at his balls with gusto.

Jack's coach was heard on the other side of the phone, "Lion! Good news!" he said.

"There were a couple of talent hunters last night, they called me earlier."

Maeve hummed her throat as she bobbed her head over Jack's length, tears running down her mascara, Cassandra for her part hefted his testicles as she kissed them a couple of times and then probed downward to his ass, where she began rimming her son.

"That's good..." Jack moaned, both at the coach and at the two sluts at his feet, his free hand petting Maeve and encouraging further down.

"Yeah... they want you for another match in a month, are you up for it?" the coach asked, Jack responded in the affirmative and the coach laughed, "If your girlfriends let you out of the bed that is..." he laughed, the gagging and moaning sounds in the background clearly heard by anyone on the other side of the line.

Jack laughed, "I'll tell them," he said with a chuckle as the gagging intensified, then said his goodbyes and as he was hanging up, Jack heard him mumble, "I don't know where he gets the strength..."

Maeve and Cassandra shared his cock for a little while longer and he dumped a load on their faces, the two then shared said load by licking and snowballing what they caught in their mouths.

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After recuperating, and drinking copious amounts of water, the sister, mommy, and girlfriends, took showers and regrouped in the kitchen, there was a feeling of awkwardness around them, but neither of the four flinched at the others touch, more like they didn't know how to interact after having a fivesome. Luckily Cassandra knew what to do.

"C'mon guys, we are all still the same people! Just more open about how much we want Jack to fuck our brians off!"

Everyone looked at her, but no one laughed, except Jack he chuckled back at her, "not helping mom."

Cassandra scoffed and slapped his shoulder jokingly, "tell him something, honey!" she said to her wife, Carine simply laughed, breaking the tension with her contagious laughter, "It was a bad joke, Cass. What do you want me to say?"

With the tension broken everyone got back in the rhythm and talked about what happened. Maty and Cecilia asked questions about when the relationships began, since when, what prompted, and more. Anne and Carine had their own questions as well. The mother-sister duo, aided by Cassandra skilfully played around mentioning Casiopea and Celeste, not sure how to handle the news that Jack had other women on the side, without him or them present, it was not long until the women got to the big news.

"... and that's when we found out we were pregnant." Anne said.

Maty was left speechless, Cecilia squeaked. The two didn't need to ask who the father was, but they still were struck by the realization of what just happened. The sudden weight on their shoulders made them tremble a little.

'

What do we do? Where do we fit in? How will this develop?

'

The two looked around to try and find Jack, but he was not in the kitchen. Both girlfriends moved around in desperation trying to find Jack, he had answers, he was in control, but he wasn't there. In the silence after the news broke, and both Maty and Cecilia instinctively held each other, a quiet noise was heard from the living room.

*

GOUGK GOUGK GOUGK

*

Cassandra held Carine, while Anne stood back, they realized the sissy and the latina needed Jack now. The three noted that although the family was naturally ok with whatever Jack wanted, maybe Cecilia and Maty never thought about children before.

Walking slowly while holding hands, Jack's girlfriends moved around the kitchen to the living room where they found their man, sitting on the couch, holding the red mane of a woman that knelt at his feet. the gagging sounds came from her, as Jack moaned and exhaled in pleasure at sheathing his cock down this woman's throat.

"Your throat makes a great sleeve, Maeve..." he said, with his eyes closed and his body reclined on the couch.

"Jack, what the fuck?" Cecilia began. He looked up and saw his two girlfriends holding hands at the threshold of the kitchen and the living room. He held Maeve down on his cock as he thought what Cecilia was talking about, then it hit him. He pointed at Maeve's head and explained she was Anne's friend before he seduced her. Cecilia let out a very loud sigh, holding her forehead with her fingers, as Maty seemed to tremble a little, on the brink of crying.

"Oh, fuck! what's going on, pets?" he asked, pulling Maeve off his cock and standing on his feet. Cecilia and Maty both exclaimed in frustration, "don't you

pets

me!"

It took a moment, and several back and forths before Jack figured out that his girlfriends were talking about the pregnancies. He quickly figured, also, that the two were more concerned than angry, two 18 year olds, in their first relationship, sharing the same man, and finding out they are also in a sexual relationship with the family of said man, and that he impregnated both mother and sister.

'

Well, what did you expect, you idiot?

' Jack told himself.

Truth be told, our lovable idiot is not familiar with all the intricacies of the interpersonal relationships he is trying to bring together. I should know after all, I'm telling you his story.

Jack turned for a moment, he heard my cackling laughter in the back of his mind, but he quickly turned back. It was more important to talk about what was happening now, than to face my amusement. He stretched his arms and held his girlfriends' shoulders, slowly guiding them to a couch different from the one Maeve was gasping and recuperating from the intense face-fuck. The latina and the sissy still gave her a quick glance before sitting down, Jack knelt at their feet.

"I need to understand this better..." he whispered, looking straight at them, "you are having sex with me, almost everyday..." he rubbed their shoulders as he talked, "unpretected sex, may I add," he cupped their faces and brought them closer, "and you just now thought about babies?"

Cecilia felt a blush coming up her cheeks, it was true... when you have sex you make babies. She just never thought about it like that before.

~'

Se Responsable...

' her mother's words came to her at that moment. She realized the gravity of the situation. '

Am I ready to be a mother? Am I willing to be involved with the children of other women?

'

She looked Jack in the eye, he was so calm... he knew, from before he understood what he was doing.

"But, Jack... how am I going to be the mother of someone else's children? How is someone else going to treat my children?" Cecilia felt terrible, tears began to fall down her face. Maty was the one to hold her.

"Jack," he whispered, "I'm not a woman, I can't have children. Yet, I'm not a man either... What kind of example am I going to be to all your children?"

The man in question got a somber look on his face, he knew this conversation was going to come up eventually. The sole complexity was too big to figure out on his own, he needed help.

Aw, yes. Help, he means the book.

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The three talked for a little while more, Jack calmed them down enough that they agreed to get in bed, it didn't help that he brought them to the master bedroom instead of his room, but they were so tired that when they flopped on the bed they lost consciousness immediately.

Anne joined the two shortly after, while Cassandra and Carine decided to stay in the kitchen keeping Maeve company. Jack went to his room and closed the door behind himself.

'

How did I miss this? My family is fine, but for everyone else...

'

He realized he was too brash, too forward. He forgot to take all possibilities into account, and one huge posibility was,

if you have sex - you get babies

. It's inevitable, unavoidable... well unless he chops his balls off with a vasectomy and gets all the medical difficulties that come with it, or he tells his girls to get protection, and they get all the medical things that come with it. Condoms are fine, he guessed... but the part of his mind that drove his greed, the same greed that became an ally when he was gunned down in that parallel timeline, the same greed that allowed him to save his sister, that greed wanted to breed every woman he fucked. It needed and demanded that mark upon the very flesh.

'

Why shouldn't I? After all, I love them... they love me...

'

It is easy to fight greed when it never gives you anything but fear and pain. The only thing that greed feeds off of is want, want and need. Up until the last timeline shift in which Anne almost died, that greed had only played a part in the writing, but never in dealing with the consequences, that was all Jack. Yet when he was shot multiple times, and he felt his life slipping from his fingers, knowing he killed his sister turned lover by his inability to write in a consistent manner, with some semblance of foreboding, it was that greed that helped him push over that final edge and close the book.

It was that greed, that painful desire to not let anything escape his grasp, to never lose anyone again, or the love that he so desperately wanted and needed, for he could never go back to that life. Never again would he live the indignity, the cold shoulder, the indifference of his original life.

'

NEVER... AGAIN...

' his mind reeled from the vice like grip greed had it under.

He took his trusty notepad, and with a pen started planning, he needed everyone to be ok with the babies, he knew Casiopea was, and Celeste was following along her cousin, he needed to make it so that anyone he brought would be ok with his mark of pregnancy on them. His desire to father the next generation was a little overwhelming at first, as he crossed names on the book replacing them with others, reading and planning, planning and reading.